Ethyl Acetate → HCID 58994988, compound

HRID 1054254Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13](Br)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[CH3:19][C:20]1([CH3:29])[CH2:25][CH2:24][C:23](B(O)O)=[CH:22][CH2:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([C:23]3[CH2:24][CH2:25][C:20]([CH3:29])([CH3:19])[CH2:21][CH:22]=3)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 4-(4-amino-3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (as prepared in the previous step, 1.45 g, 4.61 mmol), 4,4-dimethylcyclohexen-1-ylboronic acid (782 mg, 5.08 mmol) and dichloro(1,1-bisdiphenylphosphino-ferrocene palladium (II) (Pd(dppf)Cl2) dichloromethane adduct (337 mg, 0.461 mmol) in 40 mL of DMF was added K3PO4 (3.91 g, 18.4 mmol). The resulting mixture was stirred at 70° C. for 18 h under Ar. After cooling to RT, the mixture was treated with 150 mL of EtOAc, washed with H2O (3×30 mL) and brine (30 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-2% EtOAc/DCM) to afford 1.14 g (72%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C21H29NO3, 344.2 (M+H). found 344.4.

Workup

temperatureAfter cooling to RT
washwashed with H2O (3×30 mL) and brine (30 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (0-2% EtOAc/DCM)

Sources & evidence

ORD record: ord-8e464649a0a245e7a5ceedb467a05421
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394289B2

Reaction notes

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